tert-butyl N-(5-fluoro-2-hydroxy-5-(2-methyl-4-nitro-pyrazol-3-yl)cycloheptyl)carbamate → tert-butyl N-(5-[4-[[5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carbonyl]amino]-2-methyl-pyrazol-3-yl]-8-oxabicyclo[3.2.1]octan-2-yl]carbamate

Participants

Role	Name	HCID	Charge
Reactant	tert-butyl N-(5-fluoro-2-hydroxy-5-(2-methyl-4-nitro-pyrazol-3-yl)cycloheptyl)carbamate	HCID 86713008	—
Reactant	tert-butyl 4-(5-chloro-1-methyl-1H-pyrazol-4-ylcarbamoyl)-2-(2,6-difluorophenyl)thiazol-5-ylcarbamate	HCID 86713771	—
Product	tert-butyl N-(5-[4-[[5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carbonyl]amino]-2-methyl-pyrazol-3-yl]-8-oxabicyclo[3.2.1]octan-2-yl]carbamate	HCID 86713801	—

Reaction Steps

Following the procedure for Intermediate 1 starting from tert-butyl N-(5-fluoro-2-hydroxy-5-(2-methyl-4-nitro-pyrazol-3-yl)cycloheptyl)carbamate gave tert-butyl N-(5-[4-[[5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carbonyl]amino]-2-methyl-pyrazol-3-yl]-8-oxabicyclo[3.2.1]octan-2-yl]carbamate as a pale pink solid (172 mg, 17% over two steps). 1H NMR (400 MHz, CDCl3) δ 10.47 (s, 1H), 10.45 (s, 1H), 8.29 (s, 1H), 7.35-7.27 (m, 1H), 7.18-7.08 (m, 2H), 4.76 (br s, 1H), 4.29 (br s, 1H), 4.04 (br s, 1H), 3.85 (s, 3H), 2.38-2.33 (m, 1H), 2.19-1.86 (m, 7H), 1.55 (s, 9H), 1.48 (s, 9H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09328106B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-856ffd2a975a49d589c18b7bc49aff67
Source note	uspto-grants-2016_05